Pyridine → HCID 86585443, compound

HRID 1824688Notes

Reaction equation

HRID 1824688 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][C@H:8]([C:16](F)=[O:17])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:21][CH2:22][CH2:23][SH:24].C(Cl)Cl.N1C=CC=CC=1>O>[C:1]([O:5][C:6](=[O:19])[NH:7][C@H:8]([C:16](=[O:17])[NH:21][CH2:22][CH2:23][SH:24])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 9082Cysteamine HydrochlorideHCID 9965205HCID 9965205, compound

Product 1

HCID 86585443HCID 86585443, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an oven-dried, septaed 10 mL round-bottom flask, cooled under an argon atmosphere, and charged with 25m (136.0 mg, 0.51 mmol) and 2-aminoethanethiol hydrochloride (57.8 mg, 0.51 mmol) were added 2 mL freshly distilled CH2Cl2 and anhydrous pyridine (82 μL, 1.02 mmol). The reaction immediately clouded then cleared after 30 minutes. The reaction was stirred for 3 hours at room temperature, then poured into water and extracted twice with CH2Cl2. The combined CH2Cl2 extracts were washed once with 5% aqueous HCl, once with 10% aqueous sodium bicarbonate, once with saturated brine, then once with water. The organic fraction was dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to afford 123.0 mg (38% from 24m) of 26m as a colorless oil.

Workup

  1. temperaturecooled under an argon atmosphere
  2. customThe reaction
  3. extractionextracted twice with CH2Cl2
  4. washThe combined CH2Cl2 extracts were washed once with 5% aqueous HCl, once with 10% aqueous sodium bicarbonate, once with saturated brine
  5. dry with materialThe organic fraction was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4628177a952641c098c03c7afb848432
Source dataset
uspto-grants-2006_05
Patent number
US07045360B2

Reaction notes

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